November 14

A Road Trip from Boston: A Two Week Massachusetts Driving Itinerary

Destinations, USA

Road trip from Boston

Striped lighthouses, whaling ports and the oldest days of modern America.

Give Massachusetts two weeks and she will give you a salty-aired, wide-eyed look at America, with a serving of clam chowder on the side.

After this road trip from Boston, America may seem older. But you’ll feel younger.

Here’s how to make it happen.

Drive Massachusetts Map of Boston Road Trips

one Massachusetts Itinerary

It's an epic itinerary. Bookmark for now and read later

We spent two weeks driving around this compact state, spending a few days in Boston and then looping through three key areas: Salem and Cape Ann to the north of Boston, historic Plymouth, Cape Cod, Martha’s Vineyard and Nantucket to the south and then inland to endless tree-lined roads in the Berkshires.

Separate stories of the people we met and the stories we uncovered will come elsewhere on the lab, along with poetry, whimsy and the story of the invention of the first ever fried clams.

Whether you’re at the dreaming, planning or booking side of things, I present you with a nuts and bolts itinerary to help you plan your perfect road trip from Boston.

And if you’ve already been? Add in your tips below and come and say hi!

Road Trip from Boston
Road trips from Boston Massachusetts Driving Itineraries

Although, we drove through Massachusetts in this order, you can easily mix the sections around.

1 – Time in Boston

2-  Cape Ann to the north of Boston

3 – Plymouth, Cape Cod and the Islands of Martha’s Vineyard and Nantucket

4 – Inland to the Berkshires and around

1 – Boston

Days 1-3

Spend a few days in Boston recovering from jet lag and enjoying this historic, thriving, curious, famous city often overshadowed by nearby Manhattan.

Related: Things to do in Boston and beyond.

Cape Ann - Driving Massachusetts

2 - Salem and Cape Ann

 Days 3-5


It doesn’t take long after you leave Boston to see the signs of New England. It’s often hard to pinpoint exactly what that is (it’s like England but… newer!) but it’s easy to see it in Salem.

Salem’s most famous role was as the heart of the infamous Witch Trials of 1692, brought to 20th century audiences (and schoolrooms) through Arthur Miller’s The Crucible.

The Salem Witch Museum explores, in part, the story of the original trial but spends equal time talking about the idea of a “witch hunt” and how easy it is for society to mistrust and demonise “outsiders.”

This latter point brings the whole story into the 21st century and the battles fought on the news every night.

Road trip from Boston - Salem House
Tip for Family Travellers

The Salem Witch Museum really isn’t suitable for children under 8. It’s dark with screaming, animated, figures and a human-size devil, so it’s the one thing I’d recommend families take in turns or skip.

Salem itself is a pretty town worth a stop in its own right before continuing on to Cape Ann.

Driving Cape Ann Massachusetts

Cape Ann

Cape Ann is a gorgeously rural, windswept place with pebbly-sand beaches that lift the soul at dawn. Don’t expect to find tourists here, well at least not from outside America.

A stop here is all about taking in nature and local customs and really slowing down.

Travel Tip

As so many events are weather dependent (and you rarely need to book) I’d advise you look at a map and mix and match from the following. You should be able to fit everything in within a couple of days.

Watch the Sun Set at Pigeon Cove Tavern at Emerson Inn

This gorgeous spot has been entertaining guests since the 1850s when William Norwood set up a tavern for the carriage trade of the day. Ralph Waldo Emerson ("Trust thyself") and Henry David Thoreau ("I suppose that what in other men is religion is in me love of nature") used to dine here, and today it’s a beautiful New England mix of salty, polished glamour.

Appleton Farms Cape Ann Massachusetts

Appleton Farms Cape Ann Massachusetts

Spend the day at Appleton Farms

Forget any idea of what a farm means to you, and pay a visit to Appleton. It's one of the oldest continuously operating farms in America

As part of the The Trustees for Reservations group (like the National Trust in the UK – only better as they would say :) ) Appleton aims to bring the wholesome, heritage parts of farming to city slickers and those who want to get involved.

Nine generations of Appletons have worked here, amid crumbling stone walls and one of the earliest dreams of America.

It spreads over 1,000 glorious acres of rolling grasslands and maple trees, reminiscent of the resplendent scenes shown when Jed Bartlet visits his New Hampshire house in the West Wing (if that’s not giving away my age.)

It’s a working farm where you can visit livestock and also visit the historic farmhouse and hike for hours among the fields.

Catch the afternoon milking of the Jersey cows at 4:00, say hello to the chickens, goats and sheep at pretty much any time and if you’re lucky catch a cheese-making demonstration at the creamery.

Stride around in two hours or relax and make a day of it

Road Trip from Boston - Manchester on Sea Cape Ann Massachusetts

The Singing Beach at Manchester by the Sea

It’s a poetic name for a poetic place. The sea may not actually sing (it more like a whistle in your ears) but our early morning stop here really stands out as a highlight of the trip.

Where to eat in Cape Ann

Dinner or Cocktails at the 1606 Restaurant, the Beauport Hotel

Feel as though you’ve joined the much-feted East Coast Elite in the glory days of shipping by dining at 1606 Restaurant. Overlooking the sea with a nautical theme of polished wood, white walls and knotted rope, let the gentle live music convince you that you too could run for office one day…

Insider Info

Bring your appetite and try the black skillet lobster and shrimp casserole.

Road trip from Boston - Woodmans Essex Cape Ann Massachusetts

The Birthplace of Fried Clams

At the other end of the spectrum is Woodman’s of Essex, the self-proclaimed “home of the fried clam.”

It’s a lovely story in a place run by lovely people. In 1916, Lawrence “Chubby” Woodman, at the suggestion (near dare?) of a friend, decided to fry some clams ahead of the national July 4th celebrations. Over 100 years and five generations later, the clam shack is still going strong, and the legacy of the fried clam has spread across New England.

Here, you grab a seat with friends and tuck in to a range of fun, fried fare, including the state’s iconic clambake and the fresh lobster for which New England is so well known.

Road trip from Boston - Cape Ann Victoria Inn-1

Where to Stay in Cape Ann

We stayed at the Castle Manor Inn, a lovingly restored Victorian Inn just made for flowery dresses and Instagram. It’s situated inland, with soothing green gardens and that mix of grandeur and homeliness that buildings of that era exude.

While atmospheric, it’s probably not the best choice for young children as there’s no crib or soundproofing. But, if you’re travelling as a couple, it’s romantic, and if solo, a good place to chat over breakfast on the narrow terrace. And the staff couldn’t be friendlier.

Driving Cape Cod Massachusetts

3 – Plymouth, Cape Cod and the Islands

Days 5 - 11

Now it’s time to visit all those places you’ve heard about in half-whispered dreams, novels, schoolrooms, history books and anything that probes into the life of J.F.K.

Plymouth is where America began.

That’s a simplification, of course, and that statement itself is a massive understatement.

But it is where the pilgrims settled (they originally landed at the tip of Cape Cod at Provincetown), and, although not the first, it was and remains the oldest continuously inhabited settlement in the United States founded by Europeans.

Its history is fascinating and complex; its layout restfully small. It’s a walkable, beautiful grid of artsy coffee shops, bobbing boats and impressive, historic brick buildings.

But before you get there, stop off at World's End in Hingham and the cranberry bogs along the way.

Worm's End Massachusetts

World's End Massachusetts

World’s End

This unexpected wilderness between Boston and Plymouth offers a chance to get back in touch with nature and see views that haven’t changed for centuries.

Managed by the Trustees (the same ones who manage the Appleton farms), World’s End involves over 250 acres of tree-lined avenues, rocky shores, steep hills and wild grass.

Look one way to see Boston, its skyline painted in faint, pastel colours. Look the other to see a Nordic fishing village which turns out to be the New England coastline.

While the buildings of New England may be old in US terms, this place is even older.

Linked to the retreat of the same glacier that led to Boston Harbor, the salt marshes and spoon shaped hills (or drumlins) look the same now as they did thousands and thousands of years ago.

The Trustees hold concerts here on a summer’s day, but, even if grey clouds roll in, a stride between the granite ledges, red cedars and blueberry thickets make the perfect exercise break on a road trip.

Cranberry Bogs - Classic Massachusetts

Unmissable New England: The Cranberry Bogs

Yes, when I heard about cranberry bogs I wasn’t that impressed.

Yes, when I saw a photo, I completely changed my mind.

Cranberries are big business in New England, with U.S. Farmers harvesting approximately 40,000 acres of cranberries each year. What makes this farming industry so much more interesting than the rest are the shimmer of the cranberry bogs come harvest time.

Full of bright red berries as far as the eye can see, farmers flood the bogs with enough water to cover the vines that carry the berries. They then use water reels to knock the fruit off and collect them with conveyors or pumps.

Alas, for international visitors, the season is short, running from approximately mid-September to early-November each year.

We stopped off at Mayflower Cranberries LLC (call ahead if you wish to do the same) in Plympton, Massachusetts to speak to owner Jeff LaFleur.

An amiable, passionate man, LaFleur has taken cranberry farming to the next level.

A Bog With a Difference

Mayflower Cranberries LLC offers bog side dining, adopt-a-bog schemes and harvest viewing tours.

His 112-acre farm  has 236 acres of active cranberry bogs and are grower-owners for Ocean Spray Cranberries (side note – I assumed this was a big, faceless, awful corporation before this visit, but it’s actually a pretty decent co-op that benefits small farms and keeps them in trade. Jeff is a fan!)

Plymouth Massachusetts Plymouth Rock

Plymouth Massachusetts Plymouth Rock


In Plymouth, you can indulge in as much or as little history as you like. Unless you’re particularly keen, though, one full day is probably enough. Spend the day from Boston to Plymouth stopping off at World’s End and the cranberries, and then give yourself one full day in Plymouth itself before driving on to the Cape.

The Plimouth Plantation is a little way out of town, but everything else is easily walkable, and it’s really the best way to get a taste of the place.

With the big anniversary coming up in 2020 (400 years since the pilgrims landed), some places are closed for a bit of spit and polish.

So, do check in advance if there’s something you really, really want to see.

Plymouth Rock

Plymouth Rock is New England's most visited rock (drawing in more than 1million visitors each year). This historical landmark signifies the place where the Mayflower pilgrims began Plymouth Colony, which is essentially the first permanent European settlement in New England.

You'll find Plymouth Rock in the peaceful Pilgrim Memorial State Park on the shore of Plymouth Harbor. 

Wampanoag Settlement Plimouth Plantation

Wampanoag Settlement Plimouth Plantation

The Plimouth Plantation

This open-air museum really turns the traditional idea of the American thanksgiving around.

Two villages co-exist:

  • the Wampanoag settlement with trailing smoke, simmering cauldrons, feathers, paints and spears.
  • the pilgrim settlement, where actors have British accents and talk about their journey from Leiden in Holland where they were granted asylum before they left ”to find the new world.”

A Tale of Two Sides

From a fraught narrative, the Plantation showcases both sides of the American story without passing judgement. Leave at least a full afternoon to really make the most of it.

Where to Eat in Plymouth

Kiskadee Coffee Company - for local art, simple snacks and, well, good coffee.

The Water Street Café – head to this diner for an all American breakfast you’ll never forget. Order crunchy French toast and consume more calories in one sitting than you even do at Christmas. Guilty. Delicious. Fun.

Dillon’s Local – we enjoyed this so much, we went back twice. ;-)  Cosy, yet hipster eatery with classics like New England clam chowder and more modern arugula grilled peach salad.

Where to Stay in Plymouth

We stayed at the John Carver Inn & Spa, right within walking distance of town.

It’s a curious spot, with a mix of themes and styles, but rooms are spacious and well stocked. There’s a fantastically outrageous swimming pool with a full size replica of the Mayflower (with a bit of artistic license!).

After you check out, it’s time to grab your swimwear and prepare to head to the Cape…

Road Trip from Boston - 4Martha's Vineyard Massachusetts-1

Cape Cod and the Islands

This is the section of a Boston road trip that takes the most planning before you go.

But, oh my, is it worth it.

There is a spirit around the Cape that is simply unique. The curling tip of land that tickles history, the roar of the waves and the sharks that circle around. The taste of the air and the stick of the salt and the sense that adventure and the open world wait just around the corner.

And truthfully? We should have planned a little better and given ourselves more time. Not because there are so many things to do (there aren’t really), but because this is a place to slow down and not really think about things to do.

Make the Most of it

If time is tight, then follow our plan.

But if it’s not, or if you can afford to in any way, expand and relax.

​Fitting the Pieces Together For Cape Cod and the Islands

  • Station yourself in Hyannis, the hub of the Cape. While not the prettiest part, that’s a bit like saying Monet’s poppies aren’t as pretty as his waterlilies. It’s also close to the ferry port, making those connections far easier.
  • Don’t take your car to Nantucket.
  • I know I keep mentioning this,  but it’s important. Parking is tricky there and getting the car onto the ferry is even trickier.
  • I’ll write more about these areas separately, but for now, here’s the key information to help you plan your visit.
Road trip from Boston - Chatham

Cape Cod

The Cape Cod National Seashore

Managed by the National Parks Service, this area cuddles along the curve of the Cape with majestic Atlantic pine, sand and the odd shark. Arrive early as parking is limited and expensive so it makes sense to stop for a while.


Glossy, well-heeled Chatham is a delight to walk around in between its sassy book shops, art galleries and antique shops. At the “elbow” of Cape Cod, this is the point where Nantucket Sound and the Atlantic Ocean meet.

There’s easy access to a windswept sandy beach with a lighthouse that dates back to 1878. And if you’re in luck, you can catch the annual shark art festival:

Road trip from Boston - 28 Atlantic Cape Cod Massachusetts-1

Where to Eat

 Twenty-Eight Atlantic at Wequassett Resort - Fine dining with full views of the sea. Look out for the ash-roasted cod loin and Chatham shellfish company oysters.

 The children’s menu also comes as a sail on a wooden boat and table lights come inside hollowed sea urchins.

Twenty-eight Atlantic enjoys the highest ratings on Cape Cod from Forbes, AAA, and Zagat and it’s easy to see why.

28 Atlantic Cape Cod Massachusetts

Where to Stay in Hyannis

We stayed at the Anchor In, a convenient spot in Hyannis with spacious, light rooms, well-informed staff and a small outdoor pool with a view of the marina. A cosy “old New World” library serves breakfast and drinks through the day as well.

Road trip from Boston - Cape Cod Anchor In Hyannis

How to get from Hyannis to Nantucket

We travelled with Hy-line cruises. The journey is short (136 minutes) but leave plenty of time to board and book your ticket in advance.

There’s a small café on board and an easy chance to walk around for toddlers. 

Capture the Moment

Have your camera at the ready as you leave Hyannis and again as you approach Nantucket.

Road trip from Boston - Nantucket Massachusetts-1


Oh, how I loved Nantucket. I Really, really loved the place.

This small island, only 30 miles across, seems to tell the story of human innovation and reinvention through a series of picturesque beaches, stylish place to stay and chic spots to eat.

Architecturally, little has changed from the 17th century whaling hey days, all wooden slatted town houses and white columned porches.

Once it was one of the wealthiest spots in the world, thanks to its whaling industry.  

Road Trip from Boston - Abigail King in Nantucket

Today it welcomes tourists and grapples first hand with balancing the past, the future, sustainable tourism and identity. Nearly 40% of Nantucket is protected for conservation and the island is now a National Historic District to boot.

All of which sounds far too serious for what is, essentially, a gentrified beach resort. But that’s what makes it so interesting.

Visit the  Whaling Museum to uncover a striking, poignant, provocative and unapologetic look at the realities of the whaling industry and why it was so important to the world at that time.

Road trip from Boston - Whaling Museum Nantucket

Where to Eat in Nantucket

Brotherhood of Thieves - For a break from the fine dining, find pub grub and an inspiring message at the Brotherhood of Thieves.

Finding the Beach

Brant Point is a short and easy walk from Nantucket’s centre for an iconic lighthouse shot and scuff in the sand. Watch the ferries glide in and think back to the whaling past. Don’t try to swim, though. Currents here are far too strong.

The Children’s Beach is even closer to town with a playground and kids activities on in the summer.

For further beaches and exploration, hire a bike and cycle away!

Road Trip from Boston - Nantucket Massachusetts

Where to Stay in Nantucket

We stayed at 76 Main Hotel. This gorgeous little bolthole forms part of a small local chain, called/run by Lark Hotels.

Stylish inside and out, rooms are small but deliciously designed.

Road trip from Boston - 76 Main Hotel Massachusetts

There’s even a private firepit to help you embrace another Nantucket custom: melting marshmallows, biscuits and chocolate to build your own s'mores…

Road trip from Boston - Smores Nantucket
Road trip from Boston - Ferry to Martha's Vineyard-1

Martha’s Vineyard

After Nantucket, Martha’s Vineyard seems enormous and urban. But of course, she’s only 25 miles across with a population of around 17,000.

Her villages have different character, but you’ll find a key blend of summer holidays and New England in each.

You can catch the ferry from Hyannis but we drove from Hyannis and picked up the Steamship Authority ferry from Woods Hole to make the next part of the journey a little easier.

Arrive in good time to queue with your car but again, there’s a café and room to walk around when on board. And some spectacular views as you approach the island.

Road trip from Boston - Murdick's Fudge Massachusetts

What to do in Martha’s Vineyard

Again, there’ll be more detail on this but here are some highlights:

  • Look out for Murdick’s Fudge
  • Visit Tuck & Holand Metal Sculptors at the Vineyard Haven Gallery to meet the man who makes weather vanes for the stars (Steven Spielberg has a velociprator made on this very island.)
  • Feel the salt in your lungs and the wind in your hair on Martha’s sandy beaches.
  • Pay a quick visit to the pastel-pretty gingerbread cottages in Oak Bluffs.
  • Admire the wealth of the whaling captains in Edgartown, Martha’s first colonial settlement, through their Greek revival mansions.
  • Give Mad Martha’s ice cream a good licking. With a fun name like that, you may as well try one. 
Tuck & Holand Metal Sculptors at the Vineyard Haven Gallery

Where to Stay in Martha's Vineyard

The Winnetu is the kind of place I’d love to stay at all week for one of those relax-and-forget-about-the-world holidays – with children.

It’s unusual in that it is designed with families in mind – and yet it still manages to be pleasing to the eye for adults!

Rooms have decent high chairs, cots and mini self-catering facilities but with a beautiful, New England design that appeals to adults.

Winnetu Resort Martha's Vineyard

The Dunes Restaurant introduced a new concept to me: adult dining with a children’s play area within the restaurant (if you don’t have kids, don’t fear, there is an adults-only section.)

The hotel’s outdoor pool is set in spacious grounds with a lifeguard and towel service and seemed surprisingly, blissfully empty for the most part. The great, green grounds led to the ocean at South Beach where it was too blustery for us to go in but seemed majestic in its beauty.

Driving the Berkshires Massachusetts - a perfect road trip from Boston to take in Dr Seuss, Norman Rockwell, Tanglewood, Eric Carle and more. Via @insidetravellab

4 - From Martha’s Vineyard to the Berkshires and Around

Days 11 - 14

Get ready to welcome manicured, college campus America, with a side stop into the edgier Springfield, home to the Dr. Seuss Museum and the man himself. In fact, the key draw to this region (for me) was the “Iconic Illustrators Trail” – an intriguing journey through different areas of New England, each with amazing images.

Road trip from Boston - Dr Seuss Museum Springfield Massachusetts-1

But I’m getting ahead of myself. More of that in another blog post.

For now, the itinerary.

From Martha's Vineyard to Springfield

We took the ferry from Martha’s Vineyard to Woods Hole as it shortens the driving time as compared to a return ticket to Hyannis. Check which makes the most sense for you. 

Now Springfield's a town that breaks the classic New England mould and one in which I wish I had a little more time to explore.

Legendary son Dr. Seuss (real name Theodor Geisel,) grew up here amid the thriving inner-city medley of life with newly arrived immigrants from around the world.

The Amazing World of Dr. Seuss Museum showcases his career through personal artefacts, photographs and handwritten notes.

However, the real scene-stealer is the whimsical area downstairs, where characters like the Lorax greet you in life-size form.

Road trip from Boston - Adolfo Springfield Restaurant-1

Where to Stay in Springfield

We stayed at the Tower Square Hotel, a tall, slick city affair with a suite that had a separate kitchen that would have been a godsend if we’d still been weaning (it was still pretty good as we could have some family time after baby lab went to sleep in our room.)

There’s a pool with a sporty feel on one floor and an all-American breakfast available in the basement. Concierge parking and a 24-hour reception desk marked a return to city life after the blue-and-white laid-back feel of the islands.

Where to Eat in Springfield

Adolfo’s, just around the corner from the Tower Square Hotel, offers tasty, unpretentious Italian food with a local twist. Look out for the owner’s legacy on the walls…

Road trip from Boston - Eric Carle Hungry Caterpillar Museum-1

Springfield to Amherst  

If you don’t know Hungry Caterpillar Museum, this gorgeous glassy illustrator’s museum will impress. If you do, your mind and imagination may melt into happiness.

Of course, its real name is the Eric Carle Museum of Picture Book Art and it celebrates the work of illustrators across the world. The library arranges books by illustrator rather than author and there’s a huge room dedicated to getting arty and involved with crafts.

Local Flavours in Amherst

Just down the road is the Atkins Farms Country Market, a supermarket come delicatessen come restaurant that showcases the local farming produce. And it’s amazingly tasty.

Perfect for stocking up for picnics or dropping in for a bite to eat.

Road trip from Boston - Northampton

From Amherst to Northampton

This short journey only takes 20 minutes. Check in and enjoy the evening. There’s more exploring to do tomorrow.

Where to Stay in Northampton

We stayed at The Hotel Northampton. Looking for a taste of American history? This is it.

Eleanor Roosevelt, Jenny Lind, Herbert Hoover, Calvin Coolidge, Dwight Eisenhower, John F. Kennedy, and Richard Nixon all dined in the hotel's restaurant, Wiggins Tavern, in Northampton.

Rooms are moderate sized and blissfully quiet, with cots on request and a breakfast to make Americans proud.

There’s also a fantastic toy shop across the street, with the loveliest staff. They found us lightweight building blocks that stick together without glue. Perfect for travelling. Just as an aside ;-)

Where to Eat in Northampton

Bistro Les Gras - It’s a gorgeous sunset walk through Northampton to reach Bistro Les Gras, where locals dine for special occasions (they came, they chatted, they told us.)

Amid low lights and American-French charm, try the wild gulf shrimp and lemon tart. If you have a wriggly toddler with you, it’s easy to pop out and visit the live music opposite.

Iconic Illustrators Road in Massachusetts

Northampton to Stockbridge

The Norman Rockwell Museum

The museum sprawls itself across the trees and grass as all good New England complexes do. In many ways it not only tells the story of Normal Rockwell but of 20th century America as well.

Photos, paintings, and the painstakingly relocated office of the man himself offer an insight into an America that CSI Miami and the rest will never seek to touch.

Inside the Norman Rockwell Museum

Inside the Norman Rockwell Museum

Tanglewood & Lenox

The 210 acres of the Tanglewood estate were given to the Boston Symphony Orchestra in 1936 by Mary Aspinwall Tappan and the result is half stately home gardens, half rock and roll concert venue.

Even if there’s not a concert going on, you can get in and look around unless you’re unlucky and arrive as they’re setting up. 

It's in the Name

Look out for the “tangled wood,” the heaving, rising, falling, twisting trunks of the trees that gives the place its name.

Where to Eat Near Tanglewood

Lenox is another quintessential small New England town, with boutique art shops, white fences and cute places to eat.

Road trip from Boston - Historic Deerfield Massachusetts

Tanglewood to Deerfield

The last stop before returning to the hubbub of either Boston or its international airport is the leafy, quiet village of Deerfield. Here, historic mansions rise into the sky with the trees in this 18th century village that simply froze in time.

Where to Stay in Deerfield

Book in advance to stay at the Deerfield Inn, right in the heart of the historic part of Deerfield. Guest rooms wear period florals, lamps and bedspreads and the dark wooden writing desks seem from another age. 

Deerfield and Louisa May Alcott House

Deerfield and Louisa May Alcott House

Deerfield to Boston

And so, this rather epic Massachusetts road trip comes to an end.

But there’s one last stop en route to the airport: Louisa May Alcott’s house.

The author of the international bestseller published in 1868, lived here with her three sisters and parents on the outskirts of the small town of Concord.

It’s a heart-fluttering stop for literature but it also shines an interesting spotlight on society in New England at the time.

Driving Massachusetts two week itinerary via @insidetravellab

How to Make It Happen

Driving is easy in Massachusetts, even if you’re used to driving on the left. Signs are clear, fuel is easily found and all the signs are in English.

America is a country built on transport, and the love of the automobile runs deep. It is more or less expected that you’ll drive everywhere and, as a result, parking is plentiful and cheap (and public transport tends to be sporadic and awkward.)

Road trip from Boston

The key exceptions to this are in Boston (a big, old city where walking and public transport will serve you best) and the island of Nantucket (where cars are virtually forbidden.)

Access to the beaches at Cape Cod also require hefty parking fees as the place is so popular and the villages so small.

By and large, though, Massachusetts, like so much of America, is built for a fly-drive holiday.

Where and When to Pick Up Your Car

Spend a few days in Boston, soaking up the accent, the red-brown leafy streets, the education and the arty brunches.

Then pick up your car either at the airport or at one of the centres in town. Unlike most cities, Boston Logan International is quick and easy to get to, so if you plan on flying straight out at the end of the trip, then it’s cheaper and easier to drop off at the airport and go.

Car Hire With Perks: Hertz Gold

We rented a car through Hertz. The booking and collection process was simple, but what makes the service even better is that they have an American Road Trip Planner. It makes drafting itineraries so much easier.

It's perhaps not a great way of calming wanderlust, but it does mean that you can quickly plan another trip; an ideal way to beat the travel blues in my opinion

If you register with Hertz Gold Plus Rewards BEFORE you make your reservation you receive better deals, the chance to skip the queues and to use the Gold Plus Rewards counter. It's free to register and only takes 60 seconds, so it's worth doing.

What You Need to Plan in Advance

If you really have your heart set on something in particular then it makes sense to book it as soon as you can.

For me, though, most of the joy of travel involves a certain level of spontaneity and exploration, to follow where I want to go and (excuse the cheese) allow the essence of the place to appear at its own pace.

That said…in Massachusetts there are some things you really need to book in advance.

Ferries and accommodation on the islands of Martha’s Vineyard and Nantucket are often in short supply, with a fixed number of nights bookings and timetables that you need to stick to.

Leave your car behind as you head for Nantucket (leave plenty of time to find a parking space in Hyannis as it’s a bit of a scrum. Enterprising householders nearby charge a hefty fee to let you use their driveway.)

Boston can also book up quickly and so the sooner you can nail down your accommodation and car hire there, the better.

Lock these down first then work backwards from there.

Road trip from Boston - On the road in Massachusetts-1

Booking Flights to Boston

Our partner for this trip, Norwegian, has increased services to Boston with a daily non stop service between London Gatwick and Boston Airport. The flights are operated by a fleet of brand new Boeing 787 Dreamliner aircraft with two cabins in premium and economy.

Fares start from £155 one way / £259 return in economy and £415 one way / £745 return in premium, including all taxes and charges.

To book visit or call 0330 828 0854

Wifi on the Road

It would be optimistic and slightly romantic to think that mobile internet isn't needed for a road trip. It's near essential for navigation, for looking up nearby restaurants and opening times and great for contacting people back home. 

Mobile internet can be expensive, though, not to mention a pain to set up if you have to get a SIM card at the airport.

We rented a mobile wifi device (aka a MiFi) on this trip. It's really convenient for family trips because everyone can join a single device instead of replacing all your SIM cards. You also get to use your original phone number so you don't have to worry about the logistics of checking two numbers or letting loved ones back home know.

Mobile Internet from Cellhire

Cellhire is a world leader in mobile communications, allowing travellers to stay connected all over the world. The USA MiFi is one of Cellhire’s most popular products. It's well-loved for its instant data connectivity abroad, super-fast 4G speeds and its 5GB and 10GB bundles. The USA MiFi starts at as little as £50 a month.

So, is it a good idea to travel with children in Massachusetts?

Yes, a resounding, yes! People are friendly, polite, services work, healthcare is great and driving and parking is easy. This is America, after all. :)

However, while Florida and Louisiana seemed enthralled by our smallest travel companion, some (only some) areas we visited in Massachusetts seemed a little more reserved.

We were warmly welcomed at fine dining establishments, museums, on flights and in hotels but I’d just say that the difference between Massachusetts and the South was like the UK and the Med. Children are adored in the south, welcomed further north.

Driving Massachusetts with a toddler

Driving Massachusetts with a toddler

Disclosure – This trip was made up of some self-funded aspects and a mixture of paid/unpaid partnerships with Hertz, Visit Massachusetts, Norwegian, and Cellhire. As ever, all opinions remain my own. Otherwise, what is the point?!

So what do you think? What did I miss? What else would you add about road trips in Massachusetts?


Driving itinerary

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About the author

Abi King

Hi, I'm Abi, a doctor turned writer who's worked with Lonely Planet, the BBC, UNESCO and more. Find out more.

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